Almost a hundred years ago back in 1919, the 18th Amendment was passed in the USA and Prohibition became a federal law. The law officially came into effect in 1920, forcing all alcohol-related commerce to close, or find a new means of business. Although the purpose of Prohibition was to cut down on crime and boozing, the era actually prompted a new wave of gang-related crime and an elaborate underground bootlegging ring.

It was a time of chaos, and although it may be over, hundreds of collections exist across the globe to commemorate the Prohibition. The following are a few of the most valuable and unique pieces of these collections.

1926 Bottle of Scotch Whiskey

On December 8th 2007, Christie’s auction house in New York hosted their first liquor auction since before the prohibition. This Macallan scotch whiskey, bottled while booze was still illegal sold for $57,000. That’s one expensive drink!

Al Capone’s 1928 Cadillac

According to London’s Daily Mail, bootlegging king-pin and perhaps the most iconic Gangster of all time, Al Capone’s bullet-proof 1928 Cadillac sold for $37,000 in 1971. For the record, that’s $8,000 more than President John F. Kennedy’s 1963 Lincoln Continental sedan sold for.

Al Capone’s Personal Handgun

This nickel-plated, double action Colt.28 was made in May 1929. Three months earlier, Al Capone had ordered the death of seven rivals in one of the most notorious gang killings of all time: The St. Valentine’s Day Massacre.

In 2011, the same gun sold in auction for $100,000. Let’s hope the buyer only wanted it for display!

Bonnie Parker’s Revolver

Men aren’t the only ones who like to play with guns! Bonnie Parker–one half of the notorious Bonnie and Clyde, was also arrested with a Colt revolver strapped to her thigh. A copy of the note written by Frank A. Hamer (the ranger who led the team that ambushed the couple) accompanies the pistol, and reads “Bonnie was squatting on it.” Together, the artifacts are worth upwards of $150,000.

Gangster Love Letters

Even the baddest of the bad criminals showed their soft side sometimes…but such displays of vulnerability were rare, as is reflected by the high price tags on artifacts like love letters and jewellery sent by some of the worst mobsters to their family members and “special someones”. Special notes sent from prison cells and gang hideways from some of the most notorious criminals in the prohibiton era, have sold for thousands of dollars. In fact, sheet music of a love song written by Al Capone for his wife, sold for $45,000.